Tert-butyl 7-amino-4,5-dihydro-1H-benzo[D]azepine-3(2H)-carboxylate → HCID 59612456, compound

HRID 1890097Notes

Reaction equation

HRID 1890097 reaction equation
Cl[C:2]1[N:24]=[C:5]2[C:6]([C:10]3[CH:15]=[C:14]([CH:16]([F:18])[F:17])[CH:13]=[CH:12][C:11]=3[O:19][CH2:20][CH:21]([F:23])[F:22])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[C:25]([O:29][C:30]([N:32]1[CH2:38][CH2:37][C:36]2[CH:39]=[CH:40][C:41]([NH2:43])=[CH:42][C:35]=2[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26]>>[C:25]([O:29][C:30]([N:32]1[CH2:38][CH2:37][C:36]2[CH:39]=[CH:40][C:41]([NH:43][C:2]3[N:24]=[C:5]4[C:6]([C:10]5[CH:15]=[C:14]([CH:16]([F:18])[F:17])[CH:13]=[CH:12][C:11]=5[O:19][CH2:20][CH:21]([F:23])[F:22])=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)=[CH:42][C:35]=2[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:26])[CH3:27]

Participants

3

Reactant 2

HCID 11402789Tert-butyl 7-amino-4,5-dihydro-1H-benzo[D]azepine-3(2H)-carboxylateHCID 86648370HCID 86648370, compound

Product 1

HCID 59612456HCID 59612456, compound

Procedure

7-{8-[2-(2,2-difluoro-ethoxy)-5-difluoromethyl-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino}-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester was prepared from 2-chloro-8-[2-(2,2-difluoro-ethoxy)-5-difluoromethyl-phenyl]-[1,2,4]-triazolo[1,5-a]pyridine (0.182 g, 506 mmol) and 7-amino-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylic acid tert-butyl ester (0.199 g, 759 mmol) in a manner analogous to Example 311a and 311b to give product: 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.54 (s, 1H), 8.78 (d, 1H), 7.90 (s, 1H), 7.65 (m, 2H), 7.42 (m, 3H), 7.10 (br m, 1H) 7.05 (m, 2H), 6.35 (br m, 1H), 4.43 (m, 2H), 3.40 (m, 4H), 2.75 (m, 4H), 1.41 (s, 9H). MS=586 (MH)+.

Workup

  1. customto give product

Sources & evidence

ORD record
ord-2d30d20c773e44b88559a8c55d123d21
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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